Synthesis, Characterization and Cell Imaging of Water Soluble Polythiophene Derivative†

doi:10.7503/cjcu20180204

Abstract

Abstract:

A new polythiophene derivative, random copolymer of N,N,N-trimethyl-2-(2-{2-[2-(thiophen-3-yl)ethoxy]ethoxy}ethoxy)ethanaminium bromide and(4-{[2-(2-{2-[2-(thiophen-3-yl)ethoxy]ethoxy}ethoxy)ethyl]carbamoyl}phenyl)boronic acid, abbreviated as PT-2, was synthesized through FeCl₃oxidative polymerization reaction. Its optical properties and applications in cellular imaging were investigated. The UV-Vis absorption and fluorescence emission spectra were measured in water solution, the absorption maximum is 419 nm, emission maximum is 579 nm, molar absorption coefficient is 4.6×10³ L/(mol·cm), fluorescence quantum yield is 12%. Dynamic light scattering test showed that the average particle size of its aggregates formed in water was about 234 nm. Under the irradiation of mercury lamp(100 W), PT-2 exhibits a satisfactory photostability. Moreover, after co-culture with human lung cancer(A549) cells for 24 h, PT-2 shows low cytotoxicity and could be enriched in the cytoplasm. It’s fluorescence image could superposed well with lysosome-specific dye(Lyso Tracker Blue DND-22). Thus, PT-2 has potential application value in lysosomal-specific cell imaging.

Key words: Water soluble polythiophene derivative, Lysosomal-specific, Cell imaging

CLC Number:

O633.3

TrendMD:

WANG Fengyan, YAN Ni, WEI Junji, XIA Huiyun, SONG Lifang, SONG Jiale, GAO Lining, YAN Luke. Synthesis, Characterization and Cell Imaging of Water Soluble Polythiophene Derivative^†[J]. Chem. J. Chinese Universities, 2018, 39(11): 2594.

Figures/Tables 8

Scheme 1 Synthetic routes of PT-2

Fig.1 Hydrodynamic diameter distribution of 100 μmol/L PT-2 in aqueous solution

Fig.2 Normalized UV-Vis absorption(a) and fluorescent(b) emission spectra of 40 μmol/L PT-2 in aqueous solution excited at 460 nm

Fig.3 Photostability of 500 μmol/L PT-2 in aqueous solution at 100 W mercury lamp irradiation(450 nm/70 nm excitation filter)

Fig.4 Cell viability data of A549 cells at different concentrations of PT-2

Fig.5 Cellular location of PT-2 after 24 h incubation with A549 cells(A—D) Experimental group A549 cells were stained with PT-2 and nuclear dye Hoechst 33342; (A'—D') control group A549 cells were stained with Hoechst 33342; (A, A') phase contrast; (B, B') Hoechst channel; (C, C') PT-2 channel; (D, D') merged. PT-2(20 μmol/L in repeated units; excitation: 488 nm; collection: 530—630 nm; false color: orange), Hoechst 33342(nuclei stain; 10 μg/mL; excitation: 405 nm; collection: 425—475 nm; false color: blue).

Fig.6 Co-location of PT-2 and Lyso Tracker Blue DND-22 in A549 cells(A) Phase contrast; (B) DND-22; (C) PT-2; (D) overlapped image of (B) and (C). PT-2(20 μmol/L in repeated units; excitation: 488 nm; collection: 530—630 nm; false color: orange).

Fig.7 Colocalization image(A) and line series analysis of PT-2(a) and Lyso Tracker Blue DND-22(b)(B)

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